Tech Time Warp of the Week: Watch Steve Jobs and Bill Gates Play The Dating Game

The rather complicated relationship between Steve Jobs and Bill Gates spanned nearly four decades. Their love-hate affair had all the makings of a modern reality TV melodrama — an early partnership giving way to jealousy, intrigue, and alleged theft, not to mention Gates ultimately rescuing Apple from the edge of the oblivion so that Steve Jobs could rise again and eat Microsoft’s lunch.

But you may not realize that these two tech titans once played The Dating Game.

Before Apple painted Microsoft’s Windows operating system as a threat to the lives of PCs everywhere, Jobs and Gates worked hand-in-hand. In the mid-1980s, Apple needed software for the Macintosh, the machine that pushed the graphical user interface into the mainstream, and Gates was happy to supply it, realizing the power of this new machine.

In October 1983, Gates appeared at Apple’s annual sales meeting in Honolulu, which doubled as the Mac’s coming out party. This was the first time Apple showed its now famous “1984” Mac Super Bowl ad and the first time the machine was publicly shown outside the company. It was actually lowered from the rafters inside a laser cone. But Gates and Jobs supplied another classic moment. They appeared in Apple’s version of the popular 1960s show, The Dating Game (see video above).

The skit, which originated with the Apple team that built the Mac, was meant to show that outside companies were building software for this new breed of machine. “Demonstrating that there was going to be third party software for the Macintosh at launch was a key objective and essential to building support [and] enthusiasm in the sales force,” says Christopher Korody, whose company, Image Stream, produced the event.

‘To create a new standard, it takes something that’s not just a little bit different. It takes something that’s really new and really captures people’s imagination, and the Macintosh — of all the machines I’ve ever seen — is the only one that meets that standard.’

— Bill Gates

In reality, the Macintosh wasn’t yet ready for primetime. But Jobs made up for this by putting on the charm. In the faux game show, he appeared as both the show’s host and a stand-in for the “bachelor” who’s looking for a date — aka the Macintosh. The potential dates were all software makers: Lotus founder Mitch Kapor, Software Publishing’s Fred Gibbons, and, yes, Gates.

“During 1984, Microsoft expects to get half of its revenues from Macintosh software,” Gates says as he introduces himself to a beaming, floppy-haired Jobs. It was all part of what Gates would later call a “weird seduction.”

Jobs then grills Gates — AKA “software magnate #3″ — and the others, asking them questions like “When was your first date with Macintosh?,” “Describe your ideal relationship with Apple?”, and “Will Macintosh be the third industry standard?”

That last question was the big one. At the time, Jobs was obsessed with dethroning IBM, a company he likened to Big Brother. And Gates — or at least his script writer — provided the appropriate answer.

“To create a new standard, it takes something that’s not just a little bit different. It takes something that’s really new and really captures people’s imagination, and the Macintosh — of all the machines I’ve ever seen — is the only one that meets that standard,” he says.

When the announcer tells Steve he must pick a suitor, he feigns shock. The Dating Game theme music boots up again, and he starts swaying back and forth, pondering his options. He always knew how to put on a show. But eventually, he responds. “Apples are red,” he says. IBM’s blue. If Mac’s going to be the third milestone…I need all of you!”

Poor Bill. He never could capture Steve’s heart — at least not completely.